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University of Groningen

DNA-based drug carriers and dynamic proteoids with tunable properties Liu, Yun

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date: 2017

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Liu, Y. (2017). DNA-based drug carriers and dynamic proteoids with tunable properties. University of Groningen.

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DNA-based drug carriers and dynamic

proteoids with tunable properties

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The work described in this thesis was carried out at the Stratingh Institute for Chemistry, University of Groningen, The Netherlands.

This work was financially supported by the Chinese Scholarship Council.

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DNA-based drug carriers and

dynamic proteoids with tunable

properties

PhD thesis

to obtain the degree of PhD at the University of Groningen

on the authority of the Rector Magnificus Prof. E. Sterken

and in accordance with

the decision by the College of Deans. This thesis will be defended in public on

Friday 10 March 2017 at 12.45 hours

by

Yun Liu

born on 16 June 1987 in Henan, China

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Supervisors Prof. A. K. H. Hirsch Prof. A. J. Minnaard Assessment committee Prof. K. U. Loos Prof. S. Otto Prof. N. Katsonis

ISBN: 978-90-367-9509-8 (printed version)

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To

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

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Table of Contents

Chapter 1 Nucleic Acid Amphiphiles as Drug Carriers ... 1

1.1 Introduction ... 2

1.2 Self-assembled DNA nanocarriers ... 4

1.3 Amphiphilic DNA nanocarriers ... 5

1.4 Conclusions and outlook ... 11

1.5 Outline for this thesis ... 13

1.6 References ... 13

Chapter 2 Molecular Biodynamers: Dynamic Covalent Analogues of Biopolymers ... 19

2.1 From constitutional dynamic chemistry to dynamers ... 20

2.2 Molecular biodynamers: molecular/covalent dynamers with biologically relevant monomers ... 21

2.3 Molecular biodynamers: DyNAs, glycodynamers and dynamic proteoids .... 23

2.4 Conclusions and outlook ... 35

2.5 References ... 36

Chapter 3 Lipid-Modified DNAs as Solubilizers of Foscan ... 39

3.1 Introduction ... 40

3.2 Results and discussion ... 42

3.3 Conclusions ... 52

3.4 Experimental section ... 53

3.5 Contributions from co-authors ... 57

3.6 References ... 57

Chapter 4 Lipid-Modified-DNA Based Delivery System for Budesonide ... 59

4.1 Introduction ... 60

4.2 Results and disscussion ... 61

4.3 Conclusions ... 65

4.4 Experimental section ... 66

4.5 Contributions from co-authors ... 68

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Chapter 5 Proteoid Dynamers with Tunable Properties ... 71

5.1 Introduction ... 72

5.2 Results and discussion ... 73

5.3 Conclusions ... 84

5.4 Experimental section ... 85

5.5 Contributions from co-authors ... 100

5.6 References ... 100

Chapter 6 Dynamic Proteoids: Biodynamers Generated from Amino Acid- or Dipeptide-Based Monomers ... 103

6.1 Introduction ... 104

6.2 Results and discussion ... 104

6.3 Conclusions ... 116

6.4 Experimental section ... 116

6.5 Contributions from co-authors ... 125

6.6 References ... 125

Summary ... 127

Samenvatting ... 131

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